Can anyone recommend an iTunes alternative music management tool for mac that doesn’t require pretending to still use windows? Preferably free/cheap. After my iPod classic died last week I’ve followed the recommendation of others here and gone for a fiio x3. I think the sound is definitely miles better – assuming I have not brainwashed myself. Although I am still getting used to the different buttons and slightly slower response times the only big downside at the moment is that each time I add an album (as I have been in the habit of doing 3 or 4 times a week)it updates the whole library and with 110g that can take half an hour. May need to time my updates a bit better. This has encouraged me to look at managing the library better. Music monkey sounded the trick but running on mac looks unduly complicated. What do other mac users here use as an alternative to iTunes? Is it worth the effort?